(1S,2R,5S,11R,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-7,9-dien-5-ol

• ChemBase ID: 127288
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: O[C@@H]1CC2=CC=C3[C@H](CC[C@]4([C@H]3CC[C@@H]4[C@@H](C=C[C@H](C)C(C)C)C)C)[C@@]2(C)CC1
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC=C3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](C=C[C@@H](C(C)C)C)C)C)C1)C
• InChI: InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1
• InChIKey: DNVPQKQSNYMLRS-VVQHAZRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,11R,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: (1S,2R,5S,11R,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• Synonyms: Ergosterol; 3β-Hydroxy-5,7,22-ergostatriene; 5,7,22-Ergostatrien-3β-ol; Provitamin D2; Ergosterol; (3β)-麦角-5,7,22-三烯甘油-3-醇; 3β-羟基-5,7,22-麦角三烯; 维生素原 D2; 麦角固醇

Database IDs

• CAS Number: 57-87-4
• EC Number: 200-352-7
• MDL Number: MFCD00003623
• Beilstein Number: 2338604
• PubChem SID: 24868972; 162221609
• PubChem CID: 439550; 444679
• CHEBI ID: 16933
• CHEMBL: 1232562
• Chemspider ID: 392539
• MeSH Name: Ergosterol
• Unique Ingredient Identifier: Z30RAY509F
• Wikipedia Title: Ergosterol

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.6324067
• LogD (pH = 7.4): 6.632407
• Log P: 6.632407
• Molar Refractivity: 127.1317 cm^3
• Polarizability: 49.356697 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 156-158 °C(lit.); 160.0 °C; 160-163 °C
• Boiling Point: 250.0 °C
• Optical Rotation: [α]20/D -120±10°, c = 1% in chloroform; [α]23/D -127.5°, c = 1.2 in chloroform

Safety Information

• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 95%
• Impurities: ~3% water
• Empirical Formula (Hill Notation): C28H44O

DETAILS

Sigma Aldrich - 45480

Biochem/physiol Actions
Ergosterol is a biological precursor of Vitamin D2 found in cell membranes of fungi and some protists such as trypanosomes. Ergosterol may be used to study the function of anti-fungal drugs such as Amphotericin B and its analogues and to study the ergosterol biosynthesis pathway within various fungi.